Benzyl Chloride → HCID 12791027, compound

HRID 1413688Notes

Reaction equation

HRID 1413688 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][NH:6][CH2:7][P:8]([OH:11])([OH:10])=[O:9])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[C:19](=[S:21])=[O:20].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO.O>[CH2:1]([O:3][C:4](=[O:12])[CH2:5][N:6]([C:19]([S:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[CH2:7][P:8]([OH:11])([OH:10])=[O:9])[CH3:2]

Participants

7

Reactant 4

HCID 7503Benzyl ChlorideHCID 10039Carbonyl Sulfide2×HCID 10340Sodium CarbonateHCID 10965464HCID 10965464, compound

Product 1

HCID 12791027HCID 12791027, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To ethyl-N-phosphonomethylglycinate (197 g.; 1.0 mol.) dissolved in 600 ml. of water at 0° C. was added sodium carbonate (159 g.; 1.5 mol.). The resulting mixture was stirred until the gas evolution ceased. The resulting solution was added over a period of one hour to a solution of carbonyl sulfide (66 g.; 1.1 mol.) which previously had been condensed in 600 ml. of methanol at -20° C. in an ice-acetone bath. Following the addition, carbonyl sulfide was sparged through the reaction mixture for seven hours. To the mixture was added benzylchloride (171 g.; 1.0 mol.) and the resulting mixture was allowed to gradually warm to 25° C. over a period of 16 hours. The reaction mixture was then filtered and the methanol removed from the filtrate in vacuo. The residue was acidified to pH2 by the addition of concentrated hydrochloric acid. An oil separated and was extracted into 2 liters of ethylacetate. The extract was dried over sodium sulfate and concentrated in vacuo to yield a viscous oil. The oil was dried over phosphorous pentoxide in a vacuum dessicator for 48 hours to yield ethyl-N-[(benzylthio)carbonyl]-N-(phosphonomethyl)-glycinate, monohydrate (250 g.) as a yellow glass having a melting point of 56°-58° C. and the following analysis:

Workup

  1. customcondensed in 600 ml
  2. customat -20° C.
  3. customwas sparged through the reaction mixture for seven hours
  4. filtrationThe reaction mixture was then filtered
  5. customthe methanol removed from the filtrate in vacuo
  6. additionThe residue was acidified to pH2 by the addition of concentrated hydrochloric acid
  7. customAn oil separated
  8. extractionwas extracted into 2 liters of ethylacetate
  9. dry with materialThe extract was dried over sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customto yield a viscous oil
  12. dry with materialThe oil was dried over phosphorous pentoxide in a vacuum dessicator for 48 hours

Sources & evidence

ORD record
ord-97f1498a6add48f4b7f77b282544982b
Source dataset
uspto-grants-1981_02
Patent number
US04251258

Reaction notes

Loading…